#------------------------------------------------------------------------------
#$Date: 2022-08-17 01:02:59 +0300 (Wed, 17 Aug 2022) $
#$Revision: 277259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/74/1567484.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1567484
loop_
_publ_author_name
'Sun, Xi-Shang'
'Diao, Xin-Yu'
'Dong, Xiu-Qin'
'Wang, Chun-Jiang'
_publ_section_title
;
 Base-Promoted Cascade
 β-F-Elimination/Electrocyclization/Diels-Alder/Retro-Diels-Alder
 Reaction: Efficient Access to δ-Carboline Derivatives
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03166C
_journal_year                    2022
_chemical_formula_moiety         'C20 H16 F2 N2 O3'
_chemical_formula_sum            'C20 H16 F2 N2 O3'
_chemical_formula_weight         370.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                108.139(6)
_cell_angle_beta                 90.02(2)
_cell_angle_gamma                107.606(2)
_cell_formula_units_Z            8
_cell_length_a                   10.4381(4)
_cell_length_b                   17.2549(14)
_cell_length_c                   20.9737(14)
_cell_measurement_reflns_used    8085
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.1330
_cell_measurement_theta_min      2.6060
_cell_volume                     3403.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00  92.00   1.00    6.50    --   11.74-178.00-150.00   46
  2  ω    -13.00  58.00   1.00    6.50    --   11.74  37.00  30.00   71
  3  ω    -29.00  87.00   1.00    6.50    --   11.74  19.00 -60.00  116
  4  ω    -47.00  -1.00   1.00    7.00    --  -11.66  88.00-170.00   46
  5  ω    -45.00  -8.00   1.00    7.00    --   11.66 -37.00 -90.00   37
  6  ω     11.00  36.00   1.00    7.00    --   11.66 -37.00 -90.00   25
  7  ω    -21.00  14.00   1.00    7.00    --   11.66  77.00-150.00   35
  8  ω    -19.00  28.00   1.00    7.00    --   11.66  77.00  90.00   47
  9  ω    -13.00  27.00   1.00    7.00    --   11.66  37.00  30.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0326176000
_diffrn_orient_matrix_UB_12      0.0221223000
_diffrn_orient_matrix_UB_13      0.0115648000
_diffrn_orient_matrix_UB_21      -0.0048335000
_diffrn_orient_matrix_UB_22      -0.0196849000
_diffrn_orient_matrix_UB_23      0.0195687000
_diffrn_orient_matrix_UB_31      0.0133995000
_diffrn_orient_matrix_UB_32      -0.0611652000
_diffrn_orient_matrix_UB_33      -0.0021003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.044
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     978
_refine_ls_number_reflns         11981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0373P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9157
_reflns_number_total             11981
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03166c2.cif
_cod_data_source_block           8-5
_cod_original_cell_volume        3403.1(4)
_cod_database_code               1567484
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5000(15)
 0.5000(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C19(H19A,H19B), C39(H39A,H39B), C59(H59A,H59B), C32(H32A,H32B),
 C76(H76A,H76B), C24(H24A,H24B), C89(H89A,H89B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C14(H14), C2(H2), C12(H12), C3(H3), C4(H4), C6(H6),
 C15(H15), C5BA(H5BA), C35(H35), C2BA(H2BA), C0AA(H0AA), C4AA(H4AA), C29(H29),
 C33(H33), C41(H41), C81(H81), C30(H30), C8AA(H8AA), C27(H27), C1AA(H1AA),
 C2AA(H2AA), C49(H49), C57(H57), C73(H73), C92(H92), C22(H22), C9AA(H9AA),
 C3BA(H3BA), C0BA(H0BA), C4BA(H4BA), C3AA(H3AA), C34(H34), C58(H58), C71(H71)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C5AA(H5AA,H5AB,H5AC), C9BA(H9BA,H9BB,H9BC), C7BA(H7BA,
 H7BB,H7BC)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.793
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.1978(2) 1.65147(14) 0.56316(10) 0.0277(5) Uani 1 1 d . . . . .
F1 F 0.3487(2) 1.61288(14) 0.50351(10) 0.0248(5) Uani 1 1 d . . . . .
O3 O 0.4688(3) 1.87959(16) 0.54601(12) 0.0252(6) Uani 1 1 d . . . . .
O2 O 0.4954(3) 1.77412(16) 0.58070(12) 0.0295(7) Uani 1 1 d . . . . .
N2 N 0.2437(3) 1.77241(19) 0.46792(14) 0.0195(7) Uani 1 1 d . . . . .
O1 O 0.1566(3) 1.59278(16) 0.45263(12) 0.0230(6) Uani 1 1 d . . . . .
C16 C 0.3078(4) 1.7425(2) 0.50314(16) 0.0176(8) Uani 1 1 d . . . . .
C7 C -0.0812(4) 1.4886(2) 0.35669(18) 0.0256(9) Uani 1 1 d . . . . .
H7A H -0.174591 1.473320 0.336112 0.031 Uiso 1 1 calc R U . . .
H7B H -0.086393 1.472753 0.398335 0.031 Uiso 1 1 calc R U . . .
C13 C -0.1842(4) 1.6921(3) 0.29178(18) 0.0311(10) Uani 1 1 d . . . . .
H13 H -0.258689 1.683358 0.261400 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0772(4) 1.3992(3) 0.19953(18) 0.0281(10) Uani 1 1 d . . . . .
H5 H 0.084201 1.403292 0.155462 0.034 Uiso 1 1 calc R U . . .
C20 C 0.5911(4) 2.0286(2) 0.60095(19) 0.0348(10) Uani 1 1 d . . . . .
H20A H 0.584515 2.037883 0.557463 0.052 Uiso 1 1 calc R U . . .
H20B H 0.674650 2.069541 0.628052 0.052 Uiso 1 1 calc R U . . .
H20C H 0.513298 2.037079 0.624929 0.052 Uiso 1 1 calc R U . . .
N1 N -0.0155(3) 1.5810(2) 0.37396(14) 0.0206(7) Uani 1 1 d . . . . .
C8 C 0.0914(4) 1.6284(2) 0.41983(17) 0.0185(8) Uani 1 1 d . . . . .
C11 C -0.0550(4) 1.6394(3) 0.35116(18) 0.0232(9) Uani 1 1 d . . . . .
C10 C 0.0348(4) 1.7239(2) 0.38270(18) 0.0214(9) Uani 1 1 d . . . . .
C18 C 0.4332(4) 1.7984(2) 0.54709(18) 0.0235(9) Uani 1 1 d . . . . .
C19 C 0.5924(4) 1.9383(2) 0.58927(18) 0.0281(9) Uani 1 1 d . . . . .
H19A H 0.673042 1.929728 0.567019 0.034 Uiso 1 1 calc R U . . .
H19B H 0.594991 1.927235 0.632757 0.034 Uiso 1 1 calc R U . . .
C14 C -0.0962(4) 1.7751(3) 0.32239(19) 0.0285(10) Uani 1 1 d . . . . .
H14 H -0.111651 1.821392 0.311854 0.034 Uiso 1 1 calc R U . . .
C2 C 0.0524(4) 1.3856(2) 0.32736(18) 0.0256(9) Uani 1 1 d . . . . .
H2 H 0.044321 1.380660 0.371163 0.031 Uiso 1 1 calc R U . . .
C12 C -0.1654(4) 1.6215(3) 0.30474(18) 0.0286(10) Uani 1 1 d . . . . .
H12 H -0.223999 1.564561 0.283343 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1230(4) 1.3399(3) 0.28185(18) 0.0299(10) Uani 1 1 d . . . . .
H3 H 0.161458 1.303046 0.294859 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1376(4) 1.3473(3) 0.21893(18) 0.0301(10) Uani 1 1 d . . . . .
H4 H 0.188177 1.317408 0.188982 0.036 Uiso 1 1 calc R U . . .
C17 C 0.2547(4) 1.6515(2) 0.50454(17) 0.0188(9) Uani 1 1 d . . . . .
C6 C 0.0079(4) 1.4443(2) 0.24332(17) 0.0236(9) Uani 1 1 d . . . . .
H6 H -0.031548 1.480294 0.229713 0.028 Uiso 1 1 calc R U . . .
C1 C -0.0054(4) 1.4379(2) 0.30789(17) 0.0214(9) Uani 1 1 d . . . . .
C15 C 0.0134(4) 1.7922(3) 0.36774(18) 0.0254(9) Uani 1 1 d . . . . .
H15 H 0.072308 1.849263 0.388100 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1304(4) 1.7148(2) 0.42767(17) 0.0186(9) Uani 1 1 d . . . . .
F3 F 0.2601(2) 1.13707(16) 0.01075(11) 0.0295(6) Uani 1 1 d . . . . .
F6 F 0.4439(2) 1.16747(15) 0.07356(10) 0.0271(5) Uani 1 1 d . . . . .
O18 O 0.4282(3) 1.10137(16) -0.03701(13) 0.0245(6) Uani 1 1 d . . . . .
N36 N 0.5782(3) 1.07408(19) -0.11709(14) 0.0207(7) Uani 1 1 d . . . . .
O42 O 0.4607(3) 1.40162(18) 0.04947(13) 0.0307(7) Uani 1 1 d . . . . .
O48 O 0.3003(3) 1.3046(2) 0.08388(13) 0.0355(7) Uani 1 1 d . . . . .
N3 N 0.5426(3) 1.27703(19) -0.03144(14) 0.0193(7) Uani 1 1 d . . . . .
C5BA C 0.3043(4) 0.8958(2) -0.29468(18) 0.0261(9) Uani 1 1 d . . . . .
H5BA H 0.303173 0.905007 -0.337018 0.031 Uiso 1 1 calc R U . . .
C35 C 0.3099(4) 0.8686(2) -0.17176(19) 0.0224(8) Uani 1 1 d . . . . .
H35 H 0.311520 0.858468 -0.129797 0.027 Uiso 1 1 calc R U . . .
C2BA C 0.8508(4) 1.1579(3) -0.21445(17) 0.0263(10) Uani 1 1 d . . . . .
H2BA H 0.907871 1.140809 -0.247575 0.032 Uiso 1 1 calc R U . . .
C36 C 0.5270(4) 1.1295(2) -0.07317(16) 0.0183(8) Uani 1 1 d . . . . .
C5AA C 0.3090(4) 1.4836(3) 0.0539(2) 0.0464(11) Uani 1 1 d . . . . .
H5AA H 0.345810 1.499224 0.014956 0.070 Uiso 1 1 calc R U . . .
H5AB H 0.278849 1.529893 0.083043 0.070 Uiso 1 1 calc R U . . .
H5AC H 0.232259 1.430353 0.038136 0.070 Uiso 1 1 calc R U . . .
C28 C 0.6775(4) 1.1235(2) -0.14677(17) 0.0187(8) Uani 1 1 d . . . . .
C0AA C 0.7605(4) 1.0963(3) -0.19385(17) 0.0265(9) Uani 1 1 d . . . . .
H0AA H 0.755451 1.037446 -0.211248 0.032 Uiso 1 1 calc R U . . .
C4AA C 0.1993(4) 0.8225(3) -0.21906(19) 0.0275(9) Uani 1 1 d . . . . .
H4AA H 0.125357 0.781072 -0.209452 0.033 Uiso 1 1 calc R U . . .
C29 C 0.1956(4) 0.8365(2) -0.28071(19) 0.0275(10) Uani 1 1 d . . . . .
H29 H 0.118792 0.805427 -0.313002 0.033 Uiso 1 1 calc R U . . .
C33 C 0.8616(4) 1.2445(3) -0.18836(18) 0.0268(10) Uani 1 1 d . . . . .
H33 H 0.925535 1.285578 -0.203517 0.032 Uiso 1 1 calc R U . . .
C38 C 0.6844(4) 1.2108(2) -0.11822(17) 0.0174(8) Uani 1 1 d . . . . .
C39 C 0.5378(4) 0.9809(2) -0.13106(19) 0.0240(9) Uani 1 1 d . . . . .
H39A H 0.514546 0.968638 -0.088669 0.029 Uiso 1 1 calc R U . . .
H39B H 0.615963 0.961117 -0.145646 0.029 Uiso 1 1 calc R U . . .
C41 C 0.7790(4) 1.2710(2) -0.14033(17) 0.0216(9) Uani 1 1 d . . . . .
H41 H 0.786808 1.330208 -0.122391 0.026 Uiso 1 1 calc R U . . .
C53 C 0.4185(4) 0.9292(2) -0.18463(18) 0.0211(9) Uani 1 1 d . . . . .
C59 C 0.4141(4) 1.4705(3) 0.0919(2) 0.0367(11) Uani 1 1 d . . . . .
H59A H 0.491167 1.524430 0.108368 0.044 Uiso 1 1 calc R U . . .
H59B H 0.377432 1.455490 0.131618 0.044 Uiso 1 1 calc R U . . .
C61 C 0.4497(4) 1.2564(2) 0.00671(17) 0.0202(9) Uani 1 1 d . . . . .
C63 C 0.5874(4) 1.2128(2) -0.07046(16) 0.0168(8) Uani 1 1 d . . . . .
C67 C 0.3955(4) 1.1672(3) 0.01315(18) 0.0226(9) Uani 1 1 d . . . . .
C70 C 0.3929(4) 1.3212(3) 0.05084(18) 0.0242(9) Uani 1 1 d . . . . .
C81 C 0.4162(4) 0.9425(2) -0.24647(18) 0.0246(9) Uani 1 1 d . . . . .
H81 H 0.490843 0.983335 -0.256145 0.030 Uiso 1 1 calc R U . . .
F10 F 0.8869(2) 1.64377(15) 0.51352(11) 0.0320(6) Uani 1 1 d . . . . .
F12 F 0.7370(2) 1.67917(15) 0.57539(10) 0.0320(6) Uani 1 1 d . . . . .
O22 O 0.6833(3) 1.60712(16) 0.46661(12) 0.0230(6) Uani 1 1 d . . . . .
O26 O 1.0201(3) 1.8141(2) 0.57948(13) 0.0399(8) Uani 1 1 d . . . . .
O40 O 0.9584(3) 1.90621(19) 0.53935(15) 0.0460(8) Uani 1 1 d . . . . .
N43 N 0.5005(3) 1.57561(19) 0.38744(14) 0.0192(7) Uani 1 1 d . . . . .
N9 N 0.7428(3) 1.7810(2) 0.46739(14) 0.0242(8) Uani 1 1 d . . . . .
C30 C 0.5216(4) 1.4426(2) 0.26057(17) 0.0246(9) Uani 1 1 d . . . . .
H30 H 0.491305 1.484894 0.251115 0.030 Uiso 1 1 calc R U . . .
C8AA C 0.6063(4) 1.3174(2) 0.28654(17) 0.0239(9) Uani 1 1 d . . . . .
H8AA H 0.634102 1.273609 0.295064 0.029 Uiso 1 1 calc R U . . .
C27 C 0.4955(4) 1.7715(2) 0.36075(17) 0.0248(9) Uani 1 1 d . . . . .
H27 H 0.548195 1.830551 0.376991 0.030 Uiso 1 1 calc R U . . .
C1AA C 0.5799(4) 1.3939(3) 0.21265(17) 0.0254(9) Uani 1 1 d . . . . .
H1AA H 0.590987 1.403361 0.170447 0.031 Uiso 1 1 calc R U . . .
C2AA C 0.3042(4) 1.6556(2) 0.28910(19) 0.0267(9) Uani 1 1 d . . . . .
H2AA H 0.228333 1.638366 0.256948 0.032 Uiso 1 1 calc R U . . .
C9BA C 1.1919(4) 1.9820(3) 0.5400(2) 0.0543(12) Uani 1 1 d . . . . .
H9BA H 1.168778 1.987539 0.496666 0.081 Uiso 1 1 calc R U . . .
H9BB H 1.214485 1.928858 0.531990 0.081 Uiso 1 1 calc R U . . .
H9BC H 1.269688 2.031414 0.564647 0.081 Uiso 1 1 calc R U . . .
C26 C 0.5283(4) 1.7118(2) 0.38308(18) 0.0198(9) Uani 1 1 d . . . . .
C25 C 0.9454(4) 1.8296(3) 0.54495(18) 0.0317(10) Uani 1 1 d . . . . .
C32 C 0.4436(4) 1.4841(2) 0.37800(17) 0.0199(8) Uani 1 1 d . . . . .
H32A H 0.344859 1.465431 0.365619 0.024 Uiso 1 1 calc R U . . .
H32B H 0.458474 1.474261 0.421066 0.024 Uiso 1 1 calc R U . . .
C46 C 0.6061(4) 1.6326(2) 0.43018(16) 0.0176(8) Uani 1 1 d . . . . .
C48 C 0.4478(4) 1.6241(2) 0.35810(17) 0.0181(8) Uani 1 1 d . . . . .
C49 C 0.3833(4) 1.7426(2) 0.31394(18) 0.0246(9) Uani 1 1 d . . . . .
H49 H 0.359303 1.782970 0.298258 0.030 Uiso 1 1 calc R U . . .
C51 C 0.5060(4) 1.4304(2) 0.32374(16) 0.0164(8) Uani 1 1 d . . . . .
C57 C 0.6230(4) 1.3309(2) 0.22487(17) 0.0264(9) Uani 1 1 d . . . . .
H57 H 0.663456 1.297301 0.191370 0.032 Uiso 1 1 calc R U . . .
C66 C 0.6324(4) 1.7160(2) 0.43096(17) 0.0191(9) Uani 1 1 d . . . . .
C73 C 0.3349(4) 1.5944(2) 0.31071(17) 0.0207(9) Uani 1 1 d . . . . .
H73 H 0.281914 1.535359 0.294166 0.025 Uiso 1 1 calc R U . . .
C76 C 1.0774(5) 1.9794(3) 0.5794(2) 0.0529(13) Uani 1 1 d . . . . .
H76A H 1.056949 2.034204 0.589867 0.063 Uiso 1 1 calc R U . . .
H76B H 1.098469 1.971372 0.622505 0.063 Uiso 1 1 calc R U . . .
C80 C 0.8187(4) 1.7613(3) 0.50541(18) 0.0252(9) Uani 1 1 d . . . . .
C84 C 0.7828(4) 1.6747(3) 0.51391(18) 0.0250(9) Uani 1 1 d . . . . .
C92 C 0.5492(4) 1.3674(2) 0.33598(18) 0.0206(8) Uani 1 1 d . . . . .
H92 H 0.539685 1.358401 0.378409 0.025 Uiso 1 1 calc R U . . .
F13 F 0.2454(2) 0.88220(16) -0.00600(11) 0.0288(5) Uani 1 1 d . . . . .
F24 F 0.0559(2) 0.84336(15) -0.06758(10) 0.0284(5) Uani 1 1 d . . . . .
O28 O 0.0709(3) 0.90348(16) 0.04399(12) 0.0234(6) Uani 1 1 d . . . . .
O34 O 0.1014(3) 0.61816(17) -0.04271(12) 0.0266(6) Uani 1 1 d . . . . .
O38 O 0.2296(3) 0.72114(17) -0.08204(12) 0.0256(6) Uani 1 1 d . . . . .
N4 N -0.0237(3) 0.72436(19) 0.02889(14) 0.0190(7) Uani 1 1 d . . . . .
N11 N -0.0941(3) 0.91516(19) 0.11839(14) 0.0223(7) Uani 1 1 d . . . . .
C23 C -0.1887(4) 0.7745(2) 0.11072(17) 0.0209(9) Uani 1 1 d . . . . .
C22 C 0.2793(4) 1.1580(3) 0.27995(18) 0.0261(9) Uani 1 1 d . . . . .
H22 H 0.356171 1.190560 0.311965 0.031 Uiso 1 1 calc R U . . .
C9AA C -0.3788(4) 0.7235(3) 0.16930(18) 0.0309(10) Uani 1 1 d . . . . .
H9AA H -0.444955 0.677874 0.178637 0.037 Uiso 1 1 calc R U . . .
C3BA C 0.1637(4) 1.1189(2) 0.17022(18) 0.0259(9) Uani 1 1 d . . . . .
H3BA H 0.162300 1.125554 0.126951 0.031 Uiso 1 1 calc R U . . .
C0BA C -0.3760(4) 0.8079(3) 0.20016(18) 0.0306(10) Uani 1 1 d . . . . .
H0BA H -0.439010 0.818650 0.231747 0.037 Uiso 1 1 calc R U . . .
C6BA C 0.0540(4) 1.0618(2) 0.18614(18) 0.0229(9) Uani 1 1 d . . . . .
C31 C 0.1107(4) 0.8442(3) -0.00844(18) 0.0215(9) Uani 1 1 d . . . . .
C7BA C 0.0743(4) 0.4693(2) -0.0942(2) 0.0350(10) Uani 1 1 d . . . . .
H7BA H 0.114027 0.427577 -0.122796 0.053 Uiso 1 1 calc R U . . .
H7BB H -0.012690 0.462447 -0.116581 0.053 Uiso 1 1 calc R U . . .
H7BC H 0.060570 0.459350 -0.050811 0.053 Uiso 1 1 calc R U . . .
C4BA C 0.1685(4) 1.1007(2) 0.29634(19) 0.0287(10) Uani 1 1 d . . . . .
H4BA H 0.169979 1.094168 0.339633 0.034 Uiso 1 1 calc R U . . .
C3AA C -0.2864(4) 0.8766(3) 0.18710(18) 0.0285(10) Uani 1 1 d . . . . .
H3AA H -0.287271 0.933787 0.207987 0.034 Uiso 1 1 calc R U . . .
C21 C 0.0719(4) 0.7540(2) -0.00478(17) 0.0191(8) Uani 1 1 d . . . . .
C24 C 0.1689(4) 0.5596(2) -0.08249(18) 0.0239(8) Uani 1 1 d . . . . .
H24A H 0.255741 0.568388 -0.057877 0.029 Uiso 1 1 calc R U . . .
H24B H 0.187222 0.569645 -0.126058 0.029 Uiso 1 1 calc R U . . .
C34 C 0.2761(4) 1.1667(3) 0.21722(18) 0.0282(10) Uani 1 1 d . . . . .
H34 H 0.351077 1.205548 0.205783 0.034 Uiso 1 1 calc R U . . .
C43 C 0.1425(4) 0.6971(2) -0.04698(17) 0.0203(8) Uani 1 1 d . . . . .
C45 C -0.0820(4) 0.7824(2) 0.06797(16) 0.0179(8) Uani 1 1 d . . . . .
C58 C 0.0557(4) 1.0532(2) 0.24932(18) 0.0261(9) Uani 1 1 d . . . . .
H58 H -0.019979 1.014821 0.260791 0.031 Uiso 1 1 calc R U . . .
C71 C -0.2848(4) 0.7059(3) 0.12471(18) 0.0255(9) Uani 1 1 d . . . . .
H71 H -0.285290 0.648362 0.103932 0.031 Uiso 1 1 calc R U . . .
C75 C -0.0311(4) 0.8671(2) 0.07480(17) 0.0215(9) Uani 1 1 d . . . . .
C87 C -0.1947(4) 0.8579(3) 0.14183(18) 0.0240(9) Uani 1 1 d . . . . .
C89 C -0.0666(4) 1.0081(2) 0.13448(19) 0.0251(9) Uani 1 1 d . . . . .
H89A H -0.147416 1.022956 0.151726 0.030 Uiso 1 1 calc R U . . .
H89B H -0.050809 1.022917 0.092556 0.030 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O3 C19 114.8(3) . . ?
C16 N2 C9 116.3(3) . . ?
C8 O1 C17 114.9(3) . . ?
N2 C16 C18 121.1(3) . . ?
N2 C16 C17 122.5(3) . . ?
C18 C16 C17 116.3(3) . . ?
H7A C7 H7B 107.9 . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
N1 C7 C1 111.7(3) . . ?
C1 C7 H7A 109.3 . . ?
C1 C7 H7B 109.3 . . ?
C14 C13 H13 119.3 . . ?
C14 C13 C12 121.4(4) . . ?
C12 C13 H13 119.3 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C8 N1 C7 125.8(3) . . ?
C8 N1 C11 105.8(3) . . ?
C11 N1 C7 128.2(3) . . ?
O1 C8 C9 124.1(3) . . ?
N1 C8 O1 122.1(3) . . ?
N1 C8 C9 113.7(3) . . ?
N1 C11 C10 109.8(3) . . ?
N1 C11 C12 127.7(4) . . ?
C12 C11 C10 122.5(4) . . ?
C11 C10 C9 105.1(3) . . ?
C15 C10 C11 119.4(4) . . ?
C15 C10 C9 135.5(4) . . ?
O3 C18 C16 112.5(3) . . ?
O2 C18 O3 123.9(4) . . ?
O2 C18 C16 123.6(3) . . ?
O3 C19 C20 107.4(3) . . ?
O3 C19 H19A 110.2 . . ?
O3 C19 H19B 110.2 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.1(4) . . ?
C15 C14 H14 119.0 . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(3) . . ?
C13 C12 C11 116.2(4) . . ?
C13 C12 H12 121.9 . . ?
C11 C12 H12 121.9 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
F2 C17 O1 105.9(3) . . ?
F2 C17 C16 109.4(3) . . ?
F1 C17 F2 105.0(3) . . ?
F1 C17 O1 103.8(3) . . ?
F1 C17 C16 115.0(3) . . ?
O1 C17 C16 116.8(3) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C1 120.5(4) . . ?
C1 C6 H6 119.7 . . ?
C2 C1 C7 120.1(3) . . ?
C2 C1 C6 119.4(4) . . ?
C6 C1 C7 120.5(3) . . ?
C10 C15 H15 120.8 . . ?
C14 C15 C10 118.4(4) . . ?
C14 C15 H15 120.8 . . ?
N2 C9 C8 122.3(4) . . ?
N2 C9 C10 132.0(3) . . ?
C8 C9 C10 105.5(3) . . ?
C36 O18 C67 114.7(3) . . ?
C36 N36 C28 106.3(3) . . ?
C36 N36 C39 126.5(3) . . ?
C28 N36 C39 127.2(3) . . ?
C70 O42 C59 115.4(3) . . ?
C61 N3 C63 117.0(3) . . ?
C29 C5BA H5BA 120.0 . . ?
C29 C5BA C81 120.0(4) . . ?
C81 C5BA H5BA 120.0 . . ?
C4AA C35 H35 119.6 . . ?
C4AA C35 C53 120.9(4) . . ?
C53 C35 H35 119.6 . . ?
C0AA C2BA H2BA 118.9 . . ?
C0AA C2BA C33 122.1(4) . . ?
C33 C2BA H2BA 118.9 . . ?
O18 C36 N36 120.6(3) . . ?
O18 C36 C63 126.7(3) . . ?
N36 C36 C63 112.8(3) . . ?
H5AA C5AA H5AB 109.5 . . ?
H5AA C5AA H5AC 109.5 . . ?
H5AB C5AA H5AC 109.5 . . ?
C59 C5AA H5AA 109.5 . . ?
C59 C5AA H5AB 109.5 . . ?
C59 C5AA H5AC 109.5 . . ?
N36 C28 C38 108.3(3) . . ?
C0AA C28 N36 128.4(3) . . ?
C0AA C28 C38 123.2(4) . . ?
C2BA C0AA C28 117.1(4) . . ?
C2BA C0AA H0AA 121.5 . . ?
C28 C0AA H0AA 121.4 . . ?
C35 C4AA H4AA 119.9 . . ?
C35 C4AA C29 120.2(4) . . ?
C29 C4AA H4AA 119.9 . . ?
C5BA C29 C4AA 119.5(4) . . ?
C5BA C29 H29 120.2 . . ?
C4AA C29 H29 120.2 . . ?
C2BA C33 H33 120.0 . . ?
C41 C33 C2BA 120.0(4) . . ?
C41 C33 H33 120.0 . . ?
C28 C38 C63 106.2(3) . . ?
C41 C38 C28 117.4(3) . . ?
C41 C38 C63 136.4(3) . . ?
N36 C39 H39A 108.6 . . ?
N36 C39 H39B 108.6 . . ?
N36 C39 C53 114.6(3) . . ?
H39A C39 H39B 107.6 . . ?
C53 C39 H39A 108.6 . . ?
C53 C39 H39B 108.6 . . ?
C33 C41 C38 120.1(4) . . ?
C33 C41 H41 119.9 . . ?
C38 C41 H41 119.9 . . ?
C35 C53 C39 120.0(3) . . ?
C35 C53 C81 119.1(4) . . ?
C81 C53 C39 120.9(4) . . ?
O42 C59 C5AA 110.5(3) . . ?
O42 C59 H59A 109.5 . . ?
O42 C59 H59B 109.5 . . ?
C5AA C59 H59A 109.5 . . ?
C5AA C59 H59B 109.5 . . ?
H59A C59 H59B 108.1 . . ?
N3 C61 C67 123.6(3) . . ?
N3 C61 C70 121.5(3) . . ?
C70 C61 C67 114.8(3) . . ?
N3 C63 C38 132.7(3) . . ?
C36 C63 N3 120.6(3) . . ?
C36 C63 C38 106.3(3) . . ?
F3 C67 F6 105.6(3) . . ?
F3 C67 O18 103.9(3) . . ?
F3 C67 C61 114.4(3) . . ?
F6 C67 O18 106.3(3) . . ?
F6 C67 C61 110.4(3) . . ?
O18 C67 C61 115.4(3) . . ?
O42 C70 C61 110.9(3) . . ?
O48 C70 O42 124.8(4) . . ?
O48 C70 C61 124.3(4) . . ?
C5BA C81 H81 119.9 . . ?
C53 C81 C5BA 120.2(4) . . ?
C53 C81 H81 119.9 . . ?
C46 O22 C84 114.6(3) . . ?
C25 O40 C76 116.7(3) . . ?
C46 N43 C32 127.3(3) . . ?
C46 N43 C48 105.3(3) . . ?
C48 N43 C32 127.1(3) . . ?
C80 N9 C66 116.5(3) . . ?
C1AA C30 H30 119.8 . . ?
C1AA C30 C51 120.5(3) . . ?
C51 C30 H30 119.8 . . ?
C57 C8AA H8AA 119.8 . . ?
C57 C8AA C92 120.4(4) . . ?
C92 C8AA H8AA 119.8 . . ?
C26 C27 H27 120.9 . . ?
C26 C27 C49 118.1(4) . . ?
C49 C27 H27 120.9 . . ?
C30 C1AA H1AA 119.6 . . ?
C30 C1AA C57 120.8(3) . . ?
C57 C1AA H1AA 119.6 . . ?
C49 C2AA H2AA 119.4 . . ?
C73 C2AA H2AA 119.4 . . ?
C73 C2AA C49 121.2(4) . . ?
H9BA C9BA H9BB 109.5 . . ?
H9BA C9BA H9BC 109.5 . . ?
H9BB C9BA H9BC 109.5 . . ?
C76 C9BA H9BA 109.5 . . ?
C76 C9BA H9BB 109.5 . . ?
C76 C9BA H9BC 109.5 . . ?
C27 C26 C48 119.8(3) . . ?
C27 C26 C66 134.8(4) . . ?
C48 C26 C66 105.5(3) . . ?
O26 C25 O40 126.0(4) . . ?
O26 C25 C80 121.5(4) . . ?
O40 C25 C80 112.4(3) . . ?
N43 C32 H32A 109.2 . . ?
N43 C32 H32B 109.2 . . ?
N43 C32 C51 112.1(3) . . ?
H32A C32 H32B 107.9 . . ?
C51 C32 H32A 109.2 . . ?
C51 C32 H32B 109.2 . . ?
O22 C46 C66 124.2(3) . . ?
N43 C46 O22 121.1(3) . . ?
N43 C46 C66 114.6(3) . . ?
N43 C48 C26 109.8(3) . . ?
C73 C48 N43 127.8(3) . . ?
C73 C48 C26 122.5(3) . . ?
C27 C49 C2AA 121.9(4) . . ?
C27 C49 H49 119.1 . . ?
C2AA C49 H49 119.1 . . ?
C30 C51 C32 121.6(3) . . ?
C92 C51 C30 118.7(3) . . ?
C92 C51 C32 119.7(3) . . ?
C8AA C57 H57 120.4 . . ?
C1AA C57 C8AA 119.2(4) . . ?
C1AA C57 H57 120.4 . . ?
N9 C66 C26 132.7(3) . . ?
N9 C66 C46 122.3(4) . . ?
C46 C66 C26 104.8(3) . . ?
C2AA C73 C48 116.6(3) . . ?
C2AA C73 H73 121.7 . . ?
C48 C73 H73 121.7 . . ?
O40 C76 H76A 110.0 . . ?
O40 C76 H76B 110.0 . . ?
C9BA C76 O40 108.4(4) . . ?
C9BA C76 H76A 110.0 . . ?
C9BA C76 H76B 110.0 . . ?
H76A C76 H76B 108.4 . . ?
N9 C80 C25 119.0(4) . . ?
N9 C80 C84 123.0(4) . . ?
C84 C80 C25 118.0(3) . . ?
F10 C84 F12 104.5(3) . . ?
F10 C84 O22 103.8(3) . . ?
F10 C84 C80 114.9(3) . . ?
F12 C84 O22 105.9(3) . . ?
F12 C84 C80 109.6(3) . . ?
O22 C84 C80 117.1(3) . . ?
C8AA C92 H92 119.8 . . ?
C51 C92 C8AA 120.4(3) . . ?
C51 C92 H92 119.8 . . ?
C75 O28 C31 114.1(3) . . ?
C43 O34 C24 115.4(3) . . ?
C21 N4 C45 116.4(3) . . ?
C75 N11 C87 106.6(3) . . ?
C75 N11 C89 125.7(3) . . ?
C87 N11 C89 127.7(3) . . ?
C71 C23 C45 135.7(4) . . ?
C87 C23 C45 106.4(3) . . ?
C87 C23 C71 117.9(4) . . ?
C4BA C22 H22 120.3 . . ?
C34 C22 H22 120.3 . . ?
C34 C22 C4BA 119.4(4) . . ?
C0BA C9AA H9AA 120.0 . . ?
C0BA C9AA C71 120.0(4) . . ?
C71 C9AA H9AA 120.0 . . ?
C6BA C3BA H3BA 119.8 . . ?
C6BA C3BA C34 120.4(3) . . ?
C34 C3BA H3BA 119.8 . . ?
C9AA C0BA H0BA 118.5 . . ?
C3AA C0BA C9AA 123.0(4) . . ?
C3AA C0BA H0BA 118.5 . . ?
C3BA C6BA C89 120.4(3) . . ?
C58 C6BA C3BA 119.6(4) . . ?
C58 C6BA C89 119.9(4) . . ?
F13 C31 F24 105.9(3) . . ?
F13 C31 O28 103.7(3) . . ?
F13 C31 C21 114.1(3) . . ?
F24 C31 O28 107.2(3) . . ?
F24 C31 C21 110.3(3) . . ?
O28 C31 C21 115.0(3) . . ?
H7BA C7BA H7BB 109.5 . . ?
H7BA C7BA H7BC 109.5 . . ?
H7BB C7BA H7BC 109.5 . . ?
C24 C7BA H7BA 109.5 . . ?
C24 C7BA H7BB 109.5 . . ?
C24 C7BA H7BC 109.5 . . ?
C22 C4BA H4BA 119.9 . . ?
C58 C4BA C22 120.2(4) . . ?
C58 C4BA H4BA 119.9 . . ?
C0BA C3AA H3AA 121.8 . . ?
C0BA C3AA C87 116.4(4) . . ?
C87 C3AA H3AA 121.8 . . ?
N4 C21 C31 123.4(3) . . ?
N4 C21 C43 120.3(3) . . ?
C43 C21 C31 116.1(3) . . ?
O34 C24 C7BA 106.7(3) . . ?
O34 C24 H24A 110.4 . . ?
O34 C24 H24B 110.4 . . ?
C7BA C24 H24A 110.4 . . ?
C7BA C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
C22 C34 C3BA 120.4(4) . . ?
C22 C34 H34 119.8 . . ?
C3BA C34 H34 119.8 . . ?
O34 C43 C21 113.0(3) . . ?
O38 C43 O34 124.2(4) . . ?
O38 C43 C21 122.8(3) . . ?
N4 C45 C23 132.9(3) . . ?
C75 C45 N4 120.5(4) . . ?
C75 C45 C23 106.5(3) . . ?
C6BA C58 C4BA 120.0(4) . . ?
C6BA C58 H58 120.0 . . ?
C4BA C58 H58 120.0 . . ?
C23 C71 H71 120.4 . . ?
C9AA C71 C23 119.2(4) . . ?
C9AA C71 H71 120.4 . . ?
O28 C75 N11 120.9(3) . . ?
O28 C75 C45 126.7(4) . . ?
N11 C75 C45 112.5(3) . . ?
C23 C87 N11 108.1(3) . . ?
C3AA C87 N11 128.3(4) . . ?
C3AA C87 C23 123.6(4) . . ?
N11 C89 C6BA 113.4(3) . . ?
N11 C89 H89A 108.9 . . ?
N11 C89 H89B 108.9 . . ?
C6BA C89 H89A 108.9 . . ?
C6BA C89 H89B 108.9 . . ?
H89A C89 H89B 107.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C17 1.366(4) . ?
F1 C17 1.340(4) . ?
O3 C18 1.344(4) . ?
O3 C19 1.466(4) . ?
O2 C18 1.201(4) . ?
N2 C16 1.306(4) . ?
N2 C9 1.366(5) . ?
O1 C8 1.353(4) . ?
O1 C17 1.395(4) . ?
C16 C18 1.475(5) . ?
C16 C17 1.508(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N1 1.456(5) . ?
C7 C1 1.517(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(5) . ?
C13 C12 1.396(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(6) . ?
C5 C6 1.367(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.504(5) . ?
N1 C8 1.341(5) . ?
N1 C11 1.402(5) . ?
C8 C9 1.376(5) . ?
C11 C10 1.421(5) . ?
C11 C12 1.403(5) . ?
C10 C15 1.387(5) . ?
C10 C9 1.449(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C15 1.385(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(6) . ?
C2 C1 1.379(5) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.369(5) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.396(5) . ?
C15 H15 0.9500 . ?
F3 C67 1.345(4) . ?
F6 C67 1.362(4) . ?
O18 C36 1.342(4) . ?
O18 C67 1.416(4) . ?
N36 C36 1.345(5) . ?
N36 C28 1.408(5) . ?
N36 C39 1.465(4) . ?
O42 C59 1.460(4) . ?
O42 C70 1.363(5) . ?
O48 C70 1.205(5) . ?
N3 C61 1.295(5) . ?
N3 C63 1.366(4) . ?
C5BA H5BA 0.9500 . ?
C5BA C29 1.381(5) . ?
C5BA C81 1.400(5) . ?
C35 H35 0.9500 . ?
C35 C4AA 1.380(5) . ?
C35 C53 1.382(5) . ?
C2BA H2BA 0.9500 . ?
C2BA C0AA 1.373(5) . ?
C2BA C33 1.392(5) . ?
C36 C63 1.365(5) . ?
C5AA H5AA 0.9800 . ?
C5AA H5AB 0.9800 . ?
C5AA H5AC 0.9800 . ?
C5AA C59 1.468(5) . ?
C28 C0AA 1.380(5) . ?
C28 C38 1.417(5) . ?
C0AA H0AA 0.9500 . ?
C4AA H4AA 0.9500 . ?
C4AA C29 1.390(5) . ?
C29 H29 0.9500 . ?
C33 H33 0.9500 . ?
C33 C41 1.384(5) . ?
C38 C41 1.396(5) . ?
C38 C63 1.424(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C53 1.521(5) . ?
C41 H41 0.9500 . ?
C53 C81 1.387(5) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C61 C67 1.520(5) . ?
C61 C70 1.488(5) . ?
C81 H81 0.9500 . ?
F10 C84 1.347(4) . ?
F12 C84 1.363(4) . ?
O22 C46 1.360(4) . ?
O22 C84 1.404(4) . ?
O26 C25 1.205(5) . ?
O40 C25 1.329(5) . ?
O40 C76 1.495(5) . ?
N43 C32 1.457(4) . ?
N43 C46 1.335(5) . ?
N43 C48 1.406(4) . ?
N9 C66 1.362(5) . ?
N9 C80 1.307(5) . ?
C30 H30 0.9500 . ?
C30 C1AA 1.368(5) . ?
C30 C51 1.406(5) . ?
C8AA H8AA 0.9500 . ?
C8AA C57 1.386(5) . ?
C8AA C92 1.389(5) . ?
C27 H27 0.9500 . ?
C27 C26 1.383(5) . ?
C27 C49 1.388(5) . ?
C1AA H1AA 0.9500 . ?
C1AA C57 1.385(5) . ?
C2AA H2AA 0.9500 . ?
C2AA C49 1.403(5) . ?
C2AA C73 1.389(5) . ?
C9BA H9BA 0.9800 . ?
C9BA H9BB 0.9800 . ?
C9BA H9BC 0.9800 . ?
C9BA C76 1.451(6) . ?
C26 C48 1.417(5) . ?
C26 C66 1.449(5) . ?
C25 C80 1.509(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C51 1.512(5) . ?
C46 C66 1.376(5) . ?
C48 C73 1.399(5) . ?
C49 H49 0.9500 . ?
C51 C92 1.386(5) . ?
C57 H57 0.9500 . ?
C73 H73 0.9500 . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C80 C84 1.494(6) . ?
C92 H92 0.9500 . ?
F13 C31 1.353(5) . ?
F24 C31 1.360(4) . ?
O28 C31 1.409(4) . ?
O28 C75 1.339(5) . ?
O34 C24 1.455(4) . ?
O34 C43 1.330(4) . ?
O38 C43 1.225(4) . ?
N4 C21 1.293(5) . ?
N4 C45 1.379(5) . ?
N11 C75 1.347(5) . ?
N11 C87 1.412(5) . ?
N11 C89 1.467(4) . ?
C23 C45 1.431(5) . ?
C23 C71 1.411(5) . ?
C23 C87 1.404(5) . ?
C22 H22 0.9500 . ?
C22 C4BA 1.397(6) . ?
C22 C34 1.371(5) . ?
C9AA H9AA 0.9500 . ?
C9AA C0BA 1.388(5) . ?
C9AA C71 1.391(6) . ?
C3BA H3BA 0.9500 . ?
C3BA C6BA 1.385(5) . ?
C3BA C34 1.391(5) . ?
C0BA H0BA 0.9500 . ?
C0BA C3AA 1.373(6) . ?
C6BA C58 1.379(5) . ?
C6BA C89 1.512(5) . ?
C31 C21 1.512(5) . ?
C7BA H7BA 0.9800 . ?
C7BA H7BB 0.9800 . ?
C7BA H7BC 0.9800 . ?
C7BA C24 1.515(5) . ?
C4BA H4BA 0.9500 . ?
C4BA C58 1.394(5) . ?
C3AA H3AA 0.9500 . ?
C3AA C87 1.385(6) . ?
C21 C43 1.479(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C34 H34 0.9500 . ?
C45 C75 1.357(5) . ?
C58 H58 0.9500 . ?
C71 H71 0.9500 . ?
C89 H89A 0.9900 . ?
C89 H89B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C16 C18 O3 0.5(5) . . . . ?
N2 C16 C18 O2 179.6(4) . . . . ?
N2 C16 C17 F2 -102.1(4) . . . . ?
N2 C16 C17 F1 140.1(3) . . . . ?
N2 C16 C17 O1 18.2(5) . . . . ?
O1 C8 C9 N2 2.8(6) . . . . ?
O1 C8 C9 C10 179.0(3) . . . . ?
C16 N2 C9 C8 -5.4(5) . . . . ?
C16 N2 C9 C10 179.6(4) . . . . ?
C7 N1 C8 O1 4.6(5) . . . . ?
C7 N1 C8 C9 -178.0(3) . . . . ?
C7 N1 C11 C10 177.7(3) . . . . ?
C7 N1 C11 C12 -2.0(6) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?
C5 C6 C1 C7 179.4(4) . . . . ?
C5 C6 C1 C2 0.1(5) . . . . ?
N1 C7 C1 C2 116.1(4) . . . . ?
N1 C7 C1 C6 -63.3(4) . . . . ?
N1 C8 C9 N2 -174.5(3) . . . . ?
N1 C8 C9 C10 1.6(4) . . . . ?
N1 C11 C10 C15 -179.4(3) . . . . ?
N1 C11 C10 C9 -1.4(4) . . . . ?
N1 C11 C12 C13 178.6(3) . . . . ?
C8 O1 C17 F2 102.7(3) . . . . ?
C8 O1 C17 F1 -147.0(3) . . . . ?
C8 O1 C17 C16 -19.4(4) . . . . ?
C8 N1 C11 C10 2.3(4) . . . . ?
C8 N1 C11 C12 -177.4(4) . . . . ?
C11 N1 C8 O1 -179.9(3) . . . . ?
C11 N1 C8 C9 -2.5(4) . . . . ?
C11 C10 C15 C14 0.2(5) . . . . ?
C11 C10 C9 N2 175.5(4) . . . . ?
C11 C10 C9 C8 -0.1(4) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C18 O3 C19 C20 -160.8(3) . . . . ?
C18 C16 C17 F2 74.5(4) . . . . ?
C18 C16 C17 F1 -43.4(4) . . . . ?
C18 C16 C17 O1 -165.3(3) . . . . ?
C19 O3 C18 O2 0.5(5) . . . . ?
C19 O3 C18 C16 179.5(3) . . . . ?
C14 C13 C12 C11 1.3(5) . . . . ?
C2 C3 C4 C5 -2.1(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C12 C11 C10 C15 0.3(6) . . . . ?
C12 C11 C10 C9 178.3(3) . . . . ?
C3 C2 C1 C7 -179.4(3) . . . . ?
C3 C2 C1 C6 -0.1(6) . . . . ?
C4 C5 C6 C1 -1.1(6) . . . . ?
C17 O1 C8 N1 -172.4(3) . . . . ?
C17 O1 C8 C9 10.5(5) . . . . ?
C17 C16 C18 O3 -176.1(3) . . . . ?
C17 C16 C18 O2 3.0(5) . . . . ?
C6 C5 C4 C3 2.0(6) . . . . ?
C1 C7 N1 C8 -80.9(4) . . . . ?
C1 C7 N1 C11 104.6(4) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C15 C10 C9 N2 -6.9(7) . . . . ?
C15 C10 C9 C8 177.4(4) . . . . ?
C9 N2 C16 C18 178.5(3) . . . . ?
C9 N2 C16 C17 -5.1(5) . . . . ?
C9 C10 C15 C14 -177.0(4) . . . . ?
O18 C36 C63 N3 -4.6(6) . . . . ?
O18 C36 C63 C38 -179.3(3) . . . . ?
N36 C36 C63 N3 176.1(3) . . . . ?
N36 C36 C63 C38 1.5(4) . . . . ?
N36 C28 C0AA C2BA -179.3(3) . . . . ?
N36 C28 C38 C41 179.0(3) . . . . ?
N36 C28 C38 C63 0.3(4) . . . . ?
N36 C39 C53 C35 -129.6(4) . . . . ?
N36 C39 C53 C81 49.9(5) . . . . ?
N3 C61 C67 F3 -135.2(4) . . . . ?
N3 C61 C67 F6 105.9(4) . . . . ?
N3 C61 C67 O18 -14.7(5) . . . . ?
N3 C61 C70 O42 -6.0(5) . . . . ?
N3 C61 C70 O48 174.9(3) . . . . ?
C35 C4AA C29 C5BA 1.0(6) . . . . ?
C35 C53 C81 C5BA 1.0(5) . . . . ?
C2BA C33 C41 C38 -0.4(6) . . . . ?
C36 O18 C67 F3 140.9(3) . . . . ?
C36 O18 C67 F6 -107.9(3) . . . . ?
C36 O18 C67 C61 14.9(4) . . . . ?
C36 N36 C28 C0AA 178.4(4) . . . . ?
C36 N36 C28 C38 0.6(4) . . . . ?
C36 N36 C39 C53 86.6(4) . . . . ?
C28 N36 C36 O18 179.4(3) . . . . ?
C28 N36 C36 C63 -1.3(4) . . . . ?
C28 N36 C39 C53 -93.2(4) . . . . ?
C28 C38 C41 C33 0.0(5) . . . . ?
C28 C38 C63 N3 -174.7(4) . . . . ?
C28 C38 C63 C36 -1.0(4) . . . . ?
C0AA C2BA C33 C41 -0.4(6) . . . . ?
C0AA C28 C38 C41 1.1(5) . . . . ?
C0AA C28 C38 C63 -177.7(3) . . . . ?
C4AA C35 C53 C39 178.4(3) . . . . ?
C4AA C35 C53 C81 -1.1(6) . . . . ?
C29 C5BA C81 C53 0.1(6) . . . . ?
C33 C2BA C0AA C28 1.4(6) . . . . ?
C38 C28 C0AA C2BA -1.8(6) . . . . ?
C39 N36 C36 O18 -0.4(5) . . . . ?
C39 N36 C36 C63 178.8(3) . . . . ?
C39 N36 C28 C0AA -1.8(6) . . . . ?
C39 N36 C28 C38 -179.6(3) . . . . ?
C39 C53 C81 C5BA -178.5(3) . . . . ?
C41 C38 C63 N3 6.9(7) . . . . ?
C41 C38 C63 C36 -179.4(4) . . . . ?
C53 C35 C4AA C29 0.1(6) . . . . ?
C59 O42 C70 O48 0.0(5) . . . . ?
C59 O42 C70 C61 -179.2(3) . . . . ?
C61 N3 C63 C36 5.9(5) . . . . ?
C61 N3 C63 C38 178.8(4) . . . . ?
C63 N3 C61 C67 3.8(5) . . . . ?
C63 N3 C61 C70 -179.5(3) . . . . ?
C63 C38 C41 C33 178.3(4) . . . . ?
C67 O18 C36 N36 172.5(3) . . . . ?
C67 O18 C36 C63 -6.7(5) . . . . ?
C67 C61 C70 O42 170.9(3) . . . . ?
C67 C61 C70 O48 -8.2(5) . . . . ?
C70 O42 C59 C5AA -90.6(4) . . . . ?
C70 C61 C67 F3 48.0(4) . . . . ?
C70 C61 C67 F6 -71.0(4) . . . . ?
C70 C61 C67 O18 168.5(3) . . . . ?
C81 C5BA C29 C4AA -1.1(6) . . . . ?
O22 C46 C66 N9 2.2(6) . . . . ?
O22 C46 C66 C26 177.7(3) . . . . ?
O26 C25 C80 N9 -178.3(4) . . . . ?
O26 C25 C80 C84 4.1(6) . . . . ?
O40 C25 C80 N9 4.9(5) . . . . ?
O40 C25 C80 C84 -172.7(3) . . . . ?
N43 C32 C51 C30 -47.5(5) . . . . ?
N43 C32 C51 C92 132.6(4) . . . . ?
N43 C46 C66 N9 -174.5(3) . . . . ?
N43 C46 C66 C26 1.0(4) . . . . ?
N43 C48 C73 C2AA -179.5(3) . . . . ?
N9 C80 C84 F10 138.4(4) . . . . ?
N9 C80 C84 F12 -104.3(4) . . . . ?
N9 C80 C84 O22 16.2(5) . . . . ?
C30 C1AA C57 C8AA 0.0(6) . . . . ?
C30 C51 C92 C8AA -0.1(6) . . . . ?
C27 C26 C48 N43 179.7(3) . . . . ?
C27 C26 C48 C73 0.4(6) . . . . ?
C27 C26 C66 N9 -6.3(7) . . . . ?
C27 C26 C66 C46 179.0(4) . . . . ?
C1AA C30 C51 C32 179.2(4) . . . . ?
C1AA C30 C51 C92 -0.9(5) . . . . ?
C26 C27 C49 C2AA -0.2(6) . . . . ?
C26 C48 C73 C2AA -0.3(5) . . . . ?
C25 O40 C76 C9BA 86.8(5) . . . . ?
C25 C80 C84 F10 -44.1(4) . . . . ?
C25 C80 C84 F12 73.1(4) . . . . ?
C25 C80 C84 O22 -166.3(3) . . . . ?
C32 N43 C46 O22 6.8(6) . . . . ?
C32 N43 C46 C66 -176.4(3) . . . . ?
C32 N43 C48 C26 176.5(3) . . . . ?
C32 N43 C48 C73 -4.2(6) . . . . ?
C32 C51 C92 C8AA 179.8(3) . . . . ?
C46 O22 C84 F10 -144.9(3) . . . . ?
C46 O22 C84 F12 105.4(3) . . . . ?
C46 O22 C84 C80 -17.1(4) . . . . ?
C46 N43 C32 C51 -91.1(4) . . . . ?
C46 N43 C48 C26 1.9(4) . . . . ?
C46 N43 C48 C73 -178.8(3) . . . . ?
C48 N43 C32 C51 95.5(4) . . . . ?
C48 N43 C46 O22 -178.6(3) . . . . ?
C48 N43 C46 C66 -1.8(4) . . . . ?
C48 C26 C66 N9 175.0(4) . . . . ?
C48 C26 C66 C46 0.3(4) . . . . ?
C49 C27 C26 C48 -0.1(5) . . . . ?
C49 C27 C26 C66 -178.6(4) . . . . ?
C49 C2AA C73 C48 0.0(5) . . . . ?
C51 C30 C1AA C57 1.0(6) . . . . ?
C57 C8AA C92 C51 1.2(6) . . . . ?
C66 N9 C80 C25 177.7(3) . . . . ?
C66 N9 C80 C84 -4.9(5) . . . . ?
C66 C26 C48 N43 -1.4(4) . . . . ?
C66 C26 C48 C73 179.3(3) . . . . ?
C73 C2AA C49 C27 0.3(6) . . . . ?
C76 O40 C25 O26 0.3(6) . . . . ?
C76 O40 C25 C80 177.0(3) . . . . ?
C80 N9 C66 C26 -178.4(4) . . . . ?
C80 N9 C66 C46 -4.4(5) . . . . ?
C84 O22 C46 N43 -174.4(3) . . . . ?
C84 O22 C46 C66 9.2(5) . . . . ?
C92 C8AA C57 C1AA -1.1(6) . . . . ?
F13 C31 C21 N4 140.5(3) . . . . ?
F13 C31 C21 C43 -44.3(4) . . . . ?
F24 C31 C21 N4 -100.5(4) . . . . ?
F24 C31 C21 C43 74.7(4) . . . . ?
O28 C31 C21 N4 20.9(5) . . . . ?
O28 C31 C21 C43 -163.9(3) . . . . ?
N4 C21 C43 O34 -3.1(5) . . . . ?
N4 C21 C43 O38 176.8(3) . . . . ?
N4 C45 C75 O28 3.7(6) . . . . ?
N4 C45 C75 N11 -175.6(3) . . . . ?
C23 C45 C75 O28 179.7(3) . . . . ?
C23 C45 C75 N11 0.5(4) . . . . ?
C22 C4BA C58 C6BA 0.8(6) . . . . ?
C9AA C0BA C3AA C87 -1.4(6) . . . . ?
C3BA C6BA C58 C4BA -1.1(6) . . . . ?
C3BA C6BA C89 N11 120.2(4) . . . . ?
C0BA C9AA C71 C23 -1.0(5) . . . . ?
C0BA C3AA C87 N11 178.6(3) . . . . ?
C0BA C3AA C87 C23 -1.0(6) . . . . ?
C6BA C3BA C34 C22 -0.2(6) . . . . ?
C31 O28 C75 N11 -169.5(3) . . . . ?
C31 O28 C75 C45 11.4(5) . . . . ?
C31 C21 C43 O34 -178.4(3) . . . . ?
C31 C21 C43 O38 1.5(5) . . . . ?
C4BA C22 C34 C3BA -0.1(6) . . . . ?
C21 N4 C45 C23 179.1(4) . . . . ?
C21 N4 C45 C75 -6.0(5) . . . . ?
C24 O34 C43 O38 0.9(5) . . . . ?
C24 O34 C43 C21 -179.2(3) . . . . ?
C34 C22 C4BA C58 -0.2(6) . . . . ?
C34 C3BA C6BA C58 0.8(6) . . . . ?
C34 C3BA C6BA C89 -178.4(3) . . . . ?
C43 O34 C24 C7BA -157.2(3) . . . . ?
C45 N4 C21 C31 -6.4(5) . . . . ?
C45 N4 C21 C43 178.7(3) . . . . ?
C45 C23 C71 C9AA -177.9(4) . . . . ?
C45 C23 C87 N11 0.1(4) . . . . ?
C45 C23 C87 C3AA 179.9(3) . . . . ?
C58 C6BA C89 N11 -59.0(5) . . . . ?
C71 C23 C45 N4 -8.2(7) . . . . ?
C71 C23 C45 C75 176.5(4) . . . . ?
C71 C23 C87 N11 -177.4(3) . . . . ?
C71 C23 C87 C3AA 2.4(6) . . . . ?
C71 C9AA C0BA C3AA 2.4(6) . . . . ?
C75 O28 C31 F13 -146.8(3) . . . . ?
C75 O28 C31 F24 101.5(3) . . . . ?
C75 O28 C31 C21 -21.6(4) . . . . ?
C75 N11 C87 C23 0.1(4) . . . . ?
C75 N11 C87 C3AA -179.6(4) . . . . ?
C75 N11 C89 C6BA -81.8(4) . . . . ?
C87 N11 C75 O28 -179.7(3) . . . . ?
C87 N11 C75 C45 -0.4(4) . . . . ?
C87 N11 C89 C6BA 102.0(4) . . . . ?
C87 C23 C45 N4 175.0(4) . . . . ?
C87 C23 C45 C75 -0.4(4) . . . . ?
C87 C23 C71 C9AA -1.3(5) . . . . ?
C89 N11 C75 O28 3.5(5) . . . . ?
C89 N11 C75 C45 -177.2(3) . . . . ?
C89 N11 C87 C23 176.9(3) . . . . ?
C89 N11 C87 C3AA -2.8(6) . . . . ?
C89 C6BA C58 C4BA 178.1(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5000(15)
2 0.5000(15)
